


The Fake Boyfriend

by Trench_coats_and_denim_jeans



Category: Supernatural
Genre: Alternate Universe - College/University, Dean is stupid, Fake/Pretend Relationship, Fluff, but Castiel is arguably worse, so much fluff and stupidity
Language: English
Status: Completed
Published: 2014-08-09
Updated: 2014-08-09
Packaged: 2018-02-12 10:28:21
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 13,344
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2106276
Author URL: https://archiveofourown.org/users/Trench_coats_and_denim_jeans/pseuds/Trench_coats_and_denim_jeans
Summary: <blockquote class="userstuff">
              <p>Castiel Novak has become accustomed to dealing with angry men over his brother's latest conquests, but this one takes the cake. Dean Winchester's brother is only friends with Gabriel, for one, and for another this strange man wants to do something absolutely ridiculous-<br/>Pretend to date Castiel to ruin their brothers' relationship.</p><p>Castiel wants to say no but he is a broke college student and the offer of free food for at least a semester is just too good of an opportunity to pass up.</p><p>AKA: The story where everyone is in on what is actually happening but Castiel.</p>
            </blockquote>





	1. The man with the brother's complex

Castiel has been dragged into a lot of things thanks to Gabriel. However, never in his years would he have expected something this stupid. In front of him is a sophomore, a very disgruntled sophomore at that. Sure, friends of his brother’s one night stands have come to yell at him since he is younger and less dangerous, apparently, but never has it been a brother.

            “I think your brother is dating mine.” The man, something Winchester, since he’s no doubt talking about Gabriel’s friend Sam, practically growls out. His voice is low, full of rage, and Castiel would honestly be worried if it weren’t for this happening at least once a month every semester before this one.

            “Sam and Gabriel are just friends, I am fairly sure.” Castiel responds, keeping his eyes on the guy. “You can ask your brother, however, if you really want to know.”

            “He won't talk to me about Gabriel,” Winchester admits, crossing his arms over his chest and looking entirely frustrated and defeated, “He thinks I will try to hurt him or something.”

            “Hm…hard to believe he could think you have anger problems,” Castiel mumbles, “Only men who are completely sane and in control ever come to the enemy’s little brother to complain.”

            “Look, you little dick, I am worried about my brother and if you know yours I'm sure you know why.” Winchester whispers roughly and Castiel crosses his arms, leaning against his dorm room doorframe. He has to give him that, Gabriel is a pretty bad influence. However, there is no way he will tell this guy that.

            “First of all…I am older than you, so do not refer to me as that. Secondly, my brother treats yours like gold. He never does anything that can get Sam in trouble anymore, honestly, it’s the most behaved my brother has ever been. You might not like them being friends, or lovers, or whatever they are, but I am in no rush to butt in.” Castiel says, “So leave me alone.”

            “No wait, Castiel!” Winchester exclaims and Castiel tenses up. Who told him his name?

            “How do you know my name?” Castiel asks, backing further into his bedroom and behind the door.

            “Sam mentioned that Gabriel couldn’t hang out with him a few weeks ago because his brother Castiel was staying the night.” Winchester explains, “I mean…I'm sure you know my name too, right?”

            “No.” Castiel answers and sees the almost crestfallen look on Winchester’s face. No doubt fearing his precious baby brother doesn’t talk about him. “My brother and I do not discuss our friends’ siblings.”

            “…Oh…well, I'm Dean.” Winchester says, holding his hand out, “And I would appreciate it if you could help me out.”

            Castiel eyes the hand suspiciously before reaching out and shaking it, “What’s in this obvious issue of a brother complex for me?”

            “If you do what I am about to ask…I will…” Dean looks inside Castiel’s room, no doubt seeing the sparse…well…everything. Castiel and Gabriel are not exactly swimming in money. “Buy your meals for you for the rest of this semester. Possibly the rest of this year. However long it takes to do what I'm planning.”

            “Hm…alright, I'm listening. What is your plan, Winchester?”

            “We’re going to date.” Dean says and Castiel quickly pulls away and goes to slam his door shut when the taller man slams a foot in the way, “Wait, wait, wait! It will be pretend! Just listen to me!”

            “I have no interest in dating a kid.” Castiel mumbles, trying to kick the stubborn man’s foot out of his door. “Please remove yourself from my presence.”

            “ _Castiel Novak_ would you just hear me out!” Dean pleads and Castiel glares at him. “Just…pretend to date me! If we do that then I can get near Gabriel, find out if they are dating, and separate them!”

            “You obviously were not listening to me,” Castiel begins, “I told you I like Gabriel with Sam. I am not going to do anything to separate them and I do not want anything to do with someone who will.”

            “Free. Food. For. A. Year.” Dean says, prying Castiel’s door open. “I get you care about your brother, I obviously do, but he is bad for Sam and I can't just let my brother be his…”

            “Saving grace?” Castiel offers, glaring at the man as he walks into his room.

            “Yeah, yeah, that.” Dean sighs, making himself comfortable on Castiel’s bed.

            “If you want to win points with me perhaps you should show a little humility.” Castiel mumbles to himself, sitting at his desk. “…You're not going to leave are you?”

            “I'm determined to help Sam.”

            “He’s eighteen. You're, what, twenty?”

            “Twenty two…” Dean admits sheepishly.

            “Well, nonetheless, he is old enough to make his own choices.” Castiel crosses his arms, looking to Dean lounging on his bed, “Cut the apron strings, Dean.”

            “Not if cutting them results in him falling into Gabriel’s arms.” Dean huffs and Castiel sighs, staring at the apparently older man in his bed. He’s not leaving until Castiel gives in, obviously, and free food for the year would be really helpful. The guy doesn’t look too bright, so perhaps Castiel can pull his own plans and get Dean to accept their brothers’ friendship…dating life?...relationship.

He can at least drag it out until Dean gives up.

            “Tell me this, Dean Winchester, will anyone believe you are dating a guy?” Castiel asks, aware of the man’s reputation as a ladies man. He never knew his name, but Sam made it perfectly clear one weekend that his brother is, in fact, a very popular man.

            “Well, I thought about that,” Dean begins, his eyes meeting Castiel’s from across the room, “But you're pretty attractive, and college is all about experimenting.”

            “Although we will not.” Castiel adds quickly.

            “Definitely not. I am firmly into chicks. Boobs are the best thing ever.”

            “So while pretending to date me…you will be sleeping around? My brother knows everything that goes on around here and if he thinks I'm with someone who is cheating…”

            Dean sits up, stretching a little, “I can go without if it means helping Sammy.”

            “Such a martyr.” Castiel says dryly.

            “Anyways, are you in or out?”

            “As long as you do not try anything and give me food, I am in.”

            Dean grins, “Excellent. So how did we meet?”

            Castiel shrugs, “You should have all of this set up already.”

            “We met in the library, started talking, then after a few weeks I asked you out. Tonight will be our first date, so it’s not too weird we don’t touch.” Dean says and Castiel leans back in his chair.

            “I am impressed, you don’t seem the type to plan things out.”

            “I need this to work.”

            Castiel rolls his eyes, “You need a therapist for your brother complex….” He grumbles, earning a pillow to the face, “Do. _Not_. Test your luck with me, Winchester.”

            Dean scoffs, “Whatever, _Novak_. Stop saying I have a brother complex.”

            “You literally barged into a stranger’s room and asked him to do a bunch of things he doesn’t want to, including dating you and seperating your brother from his brother.” Castiel narrows his eyes, “Tell me what part of that is sane. Especially for a straight man.” He can literally see the wheels turning in Dean’s mind as the man stares blankly at him, trying to come up with an answer.

            “I…I just…I need to keep him safe.” Dean says resolutely and Castiel sighs, turning to the textbook on his desk.

            “I don’t even know you and I can already tell this is going to be awful.” He mumbles, opening the book.

            “Aww, don’t be like that, huggy bear.” Dean teases, causing Castiel’s hand to jerk in shock and tear a page in his book. “…Uh…oh…”

            Taking a deep breath to contain any homicidal urges, Castiel slowly turns in his chair to send a dark look Dean’s way, “Get. _OUT_.”

            “Right, right, um…” Dean jumps off the bed and comes up to investigate the page that is fully ripped out, “Yeah…well…I'm gonna go now. I'm also never gonna call you huggy bear again…and, while I'm at it I'm going get ready for dinner…at…um…what’s your favorite restaurant around here?”

            Castiel stays silent, staring Dean down as he tries to think of the most expensive place he can, “The steak and lobster place downtown.”

            Even if they don’t go, it’s honestly worth it just for the horrified look on Dean’s face, “Wha-? Pfft, yeah, _no_. I'm not made of money.”

            “For the both of us it would be about forty…” Castiel mumbles, looking to his ruined book, “About the same amount this book would have gotten me when I returned it later this semester, had a _page not been removed_.”

            “Hey, I cannot help it if you are some weird twenty year old-”

            “Nineteen.”

            “Okay, ninetee-wait _what_? Like…nineteen and almost twenty, nineteen, right?” Dean asks and Castiel shakes his head no.

            “Like, ‘just turned nineteen last week’, nineteen.” Castiel sighs.

            “How the hell did you assume you were older than me?” Dean huffs and Castiel shrugs.

            “I thought only a stupid child would be so messed up in his logic.” The teen explains.

            “Whoa, wow, okay…” Dean stares at him in what almost looks like awe, “So a nineteen year old in his third year of college…huh. I guess I bagged me a smart one. You do look pretty young, actually.”

            “You have ‘bagged’ nothing but an annoyed conspirator.” Castiel corrects, “So please leave my room.”

            “Right, right…” Dean begins before flashing Castiel a smile that could almost be attractive if he wasn’t so annoying, “Thanks for helping me with this.”

            “”Yes, well, you broke into my room and did not give me much choice.” Castiel points out, “I try not to agitate mentally unhealthy people in my room.”

            “I'm not crazy, don’t be such a pain.”

            “Dean, I am fairly certain I already told you to leave….”

            Dean rolls his eyes, “Yes ,yes, I’ll meet you there at…hm…four?”

            Castiel looks to him annoyed, “I have a lot of homework, Dean, I won't be done until six at least.”

            “Homework before _food_? Dude, that is just wrong.”

            “It is prioritizing and there is nothing wrong with that.”

            Dean rolls his eyes, “Oh my god I hope we break them up quickly. There’s no way anyone who knows me will think I'm dating someone with such a giant rod up their ass.”

            “And no one I know would believe I stayed with…that.” Castiel gestures to the entirety of Dean, because, well, he is literally an embodiment of everything Castiel has no interest in.

            Dean groans as loud as he can before leaving the room. Castel watches before quickly getting up and locking his door, hoping Dean does not actually return. Free food would be great but having to eat it with Dean might just be a deal breaker.

 

 


	2. The library

**Summary for the Chapter:**

> Everyone knows something Castiel doesn't because he's an adorable dumb fuck

Castiel is a fairly small guy. He’s actually nicely toned but still relatively short and all of his clothes are over-sized hand-me-downs. At nineteen he has never dated, never been hit on, and honestly is babied by pretty much everyone he knows. It’s a drawback to graduating high school at 16. Everyone sees you as a child wherever you go.

            Yesterday was the first time he met someone who truly treated him like an adult. Of course, to be fair, Castiel let him believe he was older at first but he still has yet to baby him so it remains impressive. Who is that person? Dean Winchester, the strange older brother to Sam Winchester, his own older brother’s best friend.

            Said man managed to confront him about his brother’s sexual (?) life, force his way into his room, cause him to ruin a textbook, and bribe him into a fake relationship in pretty much under an hour. He even returned later that night with food and, again, forced his way in so they could eat with each other. It was awkward, more so by the fact Dean actually bought the expensive meal Castiel asked for out of spite. They discussed Dean’s unorthodox idea and how to make it work. Castiel finally got him out around ten that night, having to resort to using harsh words. He had class in the morning and needed to study.

            Luckily it’s Thursday, the last day of classes for him this week, so when he finishes with them he goes to the library to see his friend. In all honesty he would rather go to his room and sleep, but they need to study so it’s out of the question. Heading up to the third floor of the library Castiel is greeted to a mostly empty floor. It’s the quiet floor so no one ever goes there except him and his friend. Because no one really comes up here there are actually empty study rooms they can use and discuss things in, so he’s honestly happy for the unwelcoming ambiance of the top floor.

            “Cassie!” Balthazar calls, walking up to the boy and grabbing his arm, dragging him into an empty study room as the librarian shoots them annoyed looks.

            “Balthazar, you know that she has an irascible temper.” Castiel sighs and Balthazar rolls his eyes.

            “Yes, yes, the crotchety old woman hates us even more when we actually talk outside of this room.” He waves off this fact before staring down Castiel like a parent about to scold. “So…the moose had some interesting things to tell your brother last night that he passed on to me.”

            Castiel swallows. Hard. Balthazar and Gabriel are sadly friends as well so of course Sam would tell Gabriel who would tell _Balthazar_ that Castiel is dating someone. There is no way this goes well, so he might as well go with the truth. If anyone can keep a secret it is Balthazar. “I am pretending to date Dean Winchester.” He says quietly and Balthazar literally bursts into laughter. “Balthazar…”

            “Are you _serious_ , Cassie? Of all the things I could see someone talking you into, a fake relationship was definitely not what I would guess!” Balthazar claps a hand on Castiel’s shoulder, “How, and _why_ would you say yes to that?”

            “He forced his way into my room and wouldn’t leave until I said yes,” Castiel avoids eye contact, “But he also promised to pay for all of my meals for at least this semester.”

            “Aaahhhhh, that’s how he suckered you into it.” Balthazar sighs, “Cassie, you are so…”

            “We both know I struggle every semester to buy food. This is the best thing to happen to me right now.” Castiel points out, earning him a weary look from his best friend.

            “Why does he want to _pretend_ to be in a relationship anyways?” Balthazar asks, “He has seen the movies, right? It’s better to just go right in for a real relationship. Gets you into their pants faster.”

            A small blush comes to Castiel’s cheeks, “Th-that’s…not what he wants.”

            “Oh yeah? Then what does Dean Winchester want with our nerdy Castiel Novak?”

            “He wants my help to get our brothers away from each other.” Castiel explains, shrugging, “I told him I would do it, but I truly have no intention to let him break them apart.”

            A grin spreads across Balthazar’s face, “Is my little Cassie being devious and underhanded?”

            “I wouldn’t call it that.”

            “I truly would.” Balthazar pinches Castiel’s cheeks, “Using a man’s interest in you to keep him from hurting your brother. Our little Cassie is growing up!”

            Castiel frowns and slaps his hands away, “Balthazar, Dean has no interest in me. He simply has an unhealthy brother complex.”

            “Cassie, Cassie, Cassie, how have you not seen it? Dean Winchester doesn’t care about your brothers being together, he simply wants to get into your oversized pants.” Balthazar teases, motioning to the pants that are, admittedly, hanging dangerously low on Castiel’s feet.

            “Balthazar you say that about anyone who talks to me.” Castiel sighs, “Please stop trying to lose my virginity for me.”

            “I'm just saying…you could do a lot worse than Dean Winchester.” Balthazar says and Castiel remains silent. He can't deny that, honestly, Dean Winchester is attractive and aside from the blatant brother complex he seems like a pretty decent man. Probably. “See? You agree with me.”

            “He is not…the worst partner a person could have…” Castiel mumbles before looking at him, “But I do not want to date him.”

            “Well whether you like him or not, I just want you to know this whole idea is stupid.” Balthazar says, sitting down on the tacky red couch in the room, “These sort of things only work out in movies, you know. Then again…I'm pretty sure that these things have literally only ever happened in movies.”

            “They are in written stories as well, Balthazar.” Castiel points out as he pulls out books.

            “You need to stop reading fanfiction, Castiel, one boy can only be so much of a nerd.” Balthazar teases, flashing him a grin.

            “I am perfectly fine with my nerd life, Balthazar.”

            “Try not to scare Dean off with it.”

            Castiel looks to him curiously, “How can I scare off a man who literally blackmailed me into pretending to date him?”

            “…Touché.”

            “In fact, if I could somehow scare him off with my nerd life while somehow retaining the free food, I completely would.”

            Balthazar shrugs and stretches on the couch, “As long as I don’t have to spend half of my money on you this semester, I'm good. So please do keep him around.” He looks over to Castiel as he begins highlighting things, “Just try not to get attached.”

            “The man is literally obsessive over his brother to the point of thwarting his happiness. I would not worry about me becoming attached to someone so...naive in his ways of making someone happy.”

            “So…removing all of your run around…what you are saying is ‘I would never fall in love with an idiot like that’.” Balthazar points out and Castiel sighs.

            “I was not eluding to love, but, yes. I will never become infatuated in any manner with that man.”

            “Good to know.” They soon fall into a comfortable silence for an hour or so that is only cut off by the stomping of feet coming up the stairs. Looking up they see Dean and another man running onto their floor, receiving harsh glares from the librarian. Castiel feels himself actually smile, it always amuses him when someone discovers the evil that is Ms. Flannery.

            “I almost feel sorry for Dean.” Castiel says through his smile as Dean and the mysterious guy get lectured, “Almost.”

            While being yelled at, Dean’s eyes wander until they catch Castiel’s, both of them jumping a little in surprise. Mrs. Flannery continues yelling at Dean, but despite the harsh lecture a smile comes to the man’s face, his eyes staying locked on Castiel’s.

            “Not into you my ass.” Balthazar scoffs, making Castiel look away to stare at him.

            “Stop it.” Castiel warns and when he looks away from the shit eating grin on Balthazar’s face he sees Dean and the strange man coming into their study room.

            “Well hello there, Castiel.” Dean greets, flashing him a cheeky smile before looking to Balthazar, “Hello Balthazar.”

            Castiel tenses up, eying the two of them suspiciously, “How does he know your name?”

            Balthazar shoots him a guilty look that Dean mirrors, “Um…shared class?” He offers and Castiel narrows his eyes.

            “Balthazar.”

            “Dean may or may not have come to me asking who you were.” He admits, earning a harsh look from Dean.

            “I had to make sure you were Gabriel’s brother.” Dean admits, looking to Balthazar wearily, “I’m assuming you told him the truth?”

            “Yes, of course.” Castiel says, staring Dean down, “You should have told me about talking to Balthazar last night.”

            The older man plops down in a chair and shrugs, “It didn’t come up.”

            “You were there almost all night and it didn’t come up.” Castiel mutters unconvinced.

            “I'm Benny, by the way.” The man next to Balthazar says, waving his hand to get Castiel’s attention. “You fake lovers sure have the act down.” He teases and Castiel notices an almost panicked look on Dean’s face.

            “Benny…” Dean warns, “Why don’t you sit down?”

            Benny just shrugs and sits beside Balthazar, the two sharing a look Castiel doesn’t quite recognize, “Alright, so what are you two doing?”

            “Homework.” Castiel answers and Balthazar shrugs.

            “Getting help from my favorite little study buddy.”

            Dean looks at Castiel amused, “You're some kind of genius, right?”

            “A sixteen year old college student is not exactly any form of ‘genius’ to phone home about.” Castiel mumbles, back to staring at his book. “But I am fairly smart. Why?”

            “Well, I would absolutely love a tutor.” Dean leans back in his chair, putting his feet on the table until Castiel glares at him to move them off. “So why don’t you tutor me during our, what did you call them, ‘self-imposed dinners’?”

            “Alright, fine, I will tutor you.” Castiel acquiesces, “I will pretend to date you, I will tutor you, and I will eat dinner with you.”

            “Well now you are just making me sound needy.” Dean grins, “But yes. That is all I ask of you.” He leans forward in his seat, “You can ask for stuff too, outside of food.”

            Castiel raises a brow, “I do not wish for anything from you, Dean. Aside from perhaps giving my brother a chance, but you will not do that.” He sees Dean wince and feels a strange sense of accomplishment over it.

            “Anything else, though. I promise.”

            The room falls silent for a moment before Castiel looks down at his clothes, contemplating. “…Clothes…” He mumbles to himself and quickly regrets it, “No, wait, I did not mean that.”

            “New wardrobe, huh?” Dean asks, his eyes roaming over Castiel, “Yeah, we can do that. Let’s definitely do that.” He looks at him and seems to notice the guilt in Castiel’s eyes, making him add, “Don’t worry, I have a job. This is nothing for me.”

            Balthazar leans over to Benny and stage whispers, “Did he just brag on himself?”

            Benny smirks at the two, “I believe you could actually refer to it as peacocking.”


	3. A date to forget

**Summary for the Chapter:**

> Everyone's an idiot, who decided to let these people spend time together?

Tonight is the night of their double date. Well, it is technically not a date in any way but appearances. Gabriel and Sam are not dating and Castiel and Dean are _definitely_ not dating. Not for real at least. Despite it being fake, though, it’s still Castiel’s first date and he is very nervous. The add-on of it being fake is even worse. Does he complement Dean or not? If they hold hands….

Will they hold hands?

He hopes they don’t hold hands.

Not to mention Balthazar keeps mocking him about it ever since he met Dean yesterday. That was awkward. Hopefully they never have to do that again, although Balthazar desperately wants to, Castiel cannot say he is keen on the idea of sitting there with Dean as Balthazar and Benny elude to them actually dating. It makes Dean awkward, it makes Castiel awkward, and it makes the other two far too amused. He _really_ needs to reassess how he makes friends. Apparently blindly accepting anyone who wants to is not the way to go.

            A knock comes to his door along with an almost nervous sounding “Hello?”

            “Dean?” Castiel asks, opening the door to see the man standing there in a nice shirt and pants, looking undeniably out of his element. “Hello.”

            Dean does a quick once over, making Castiel worried about his own outfit. Is a dress shirt and slacks too much? Should he have asked Balthazar? No, no, he would have dressed him in something more ridiculous. “You look…” Castiel tenses up, “Nice.”

            “Really?” He asks, looking down at his outfit unsure, “This is normal for a date?”

            Dean smiles at him, a hint of sympathy in his eyes that annoys Castiel, “That’s right, this is your first date isn’t it?” His eyes widen a little, “First, erm, you know, fake date. But it’s still…your…first…form of a…date…”

            Castiel stares at him, “Yes, Dean, that is precisely what it is. Although it could have been worded more eloquently.”

            “Not all of us can be you, Castiel.” Dean rolls his eyes before settling them on Castiel with amusement, “I suppose you have some concerns, don’t you?”

            “Yes.” Castiel admits, “What is expected on a first date?” He asks curiously, “Is there a lot of touching? Hand holding? ….Kissing?”

            Dean stares at him for a moment before clearing his throat and speaking up, “Don’t worry, I will make the moves you just go with them. Everyone knows you have never dated, so it wouldn’t be so weird if,” He begins, his eyes going to Castiel’s mouth, “I took the lead.”

            “That makes sense.” Castiel agrees, moving past him towards the door. “Are they meeting us there or are we going together?”

            “Oh, um, meeting us there.” Dean says, turning towards him, “I figured we could take my impala.”

            “Seems fair enough.” Castiel mumbles, heading out the door.

            The drive there is quiet, Dean’s music playing through the awkward silence. When they finally get there and exit the car, Dean swoops in and wraps an arm around his shoulders.

            “Alright, Castiel, let’s do this.” Dean grins at him, leading them to the movie theater where Castiel notices his brother talking to Sam at the concession stand. The way he’s looking at Sam is something Castiel has gotten used to since meeting the younger Winchester. It’s a look his brother has never given anyone before, something comparable to how he looks at Castiel but with a little extra emotion that the younger Novak knows his brother isn’t ready to face yet.

            “You realize this plan of yours might actually help them get together, right?” Castiel asks and Dean tenses up.

            “They won't.”

            “They will.”

            “Shut up, Cas.” Dean grumbles as he pays their way.

            “I'm simply sayi-wait what?” Castiel asks, allowing himself to be dragged to the concession stand, “What’s a ‘Cas’?”

            “You're a Cas.” Dean explains, grabbing them popcorn and drinks.

            “Hm, that is admittedly a new nickname.” Castiel mumbles before looking at the food and drinks and tickets, “Dean…did you just pay for everything?”

            “Wow, for such a smart guy you’re not very observant are you?” Dean teases, “I figured me paying for all these dates was part of the deal.”

            “Are you secretly rich, Dean?”

            “No.”

            Castiel looks at him annoyed, “Than if you paid for all of them you would go broke.”

            Dean shoots him a wry smile, immediately making him regret saying anything, “Just how many dates do you want to go on, Cas?”

            “What? No, no, that’s not-”

            “Cassie!” Gabriel calls, running over and unknowingly saving Castiel from embarrassment.

First time that’s happened.

“Hello, Gabriel.” Castiel greets as his brother looks to Dean.

            “So, you're dating my brother, huh?”

            “Yep, it’s been a few days now.” Dean says, surprisingly calm. Or maybe it’s not a surprise? Castiel is unsure of how people deal with the siblings of the person they are dating. On TV they are never so calm.

            “How far have you gotten?” Gabriel asks, quickly catching the cup Castiel almost drops. “Careful little brother, don’t make a mess.”

            “We’ve had dates, but nothing more.” Dean assures him as they head to the theater.

            “I see. Well Cassie has never dated before so you better be nice to him or I’ll have moose here get you back.” Gabriel says and Castiel notices the fond smile on Sam’s face at the nickname. He’s obviously smitten with Gabriel. Literally _no one_ would want that nickname.

            “Threatening me with my own brother?” Dean scoffs, “Please.”

            Sam shrugs, “I like Castiel so I would do it.” He says, flashing a smile at Castiel who easily returns it. The two of them have a lot in common, and while they are not overly close they have a sort of friendship between them.

            “Damn Novaks need to back off from my brother.” Dean grumbles.

            “I assure you I have no interest in your brother, Dean.” Castiel says and Sam smirks.

            “That’s right, he’s interested in the older Winchester. Right, Castiel?” He teases.

            “Oh, um, yes.” Castiel nods, “That is correct. I am interested in Dean, and Dean alone.”

            Sam smiles at him, “I'm glad such a good person has taken interest in my brother.”

            “Your brother is a good person,” Castiel assures him, “He just has very strange logic.”

            “It’s not strange.” Dean grumbles as he sits on the inside of a row with Castiel, Gabriel moving past Sam to sit by his little brother.

            “So when did you meet Cassie?” Gabriel asks, not-so-subtly staring the two of them down.

            Dean proceeds to tell the story they made up, including fake dates to coffee shops and their shared dinners, until the previews come on. They all sit in silence, waiting for The Conjuring to start. Dean explained the night before why it had to be a horror movie by saying couples like to use the fear as an excuse to touch. Honestly, the more Castiel thinks about it the more he is sure this whole plan is going to drive Gabriel and Sam into each other’s arms.

            The movie is good, and honestly a little scary, but scarier than anything in the film is the moment Dean reaches over and grabs hold of his hand. Castiel tenses up and focuses on calming himself down after the foreign intimacy. And yes, for the record, he is aware of how pathetic the fact that hand holding makes him so nervous is. It’s a simple gesture though, their hands aren’t even laced or anything, Dean is simply cupping Castiel’s hand in his own. Heavens knows if it was more Castiel would probably have a heart attack.

            He knows Gabriel is still watching them, and occasionally he can feel Sam’s eyes on them as well. It’s strange, being judged for something he technically isn’t even doing. Getting Sam’s hopes up, making Gabriel worry, all to keep them from getting too close when in fact they are only growing closer from this whole thing. Dean truly needs to think his plans through better, but Castiel won't tell him because-you know-free food.

            “AAHHHH!” A girl screams at a particularly frightening scene right behind Castiel, making him let out a small gasp and jump a little. He can hear Dean laugh quietly, looking at Castiel amused. Suddenly it finally clicks why people actually go to movies for dates. Sitting next to each other, even in a large theater full of people, a couple can have their own intimate moments. Smiles no one else can see, whispers no one else can hear, touches no one else cares to notice. As Castiel shoots Dean a weak smile, ignoring Gabriel and Sam’s regained attention, he almost wishes he could go to a movie with Dean alone.

            But that would be a date. A real date. Dean doesn’t date men and Castiel doesn’t date anyone. Friends can go to movies together, can't they? Gabriel and Sam do, but then again they aren’t the best example. Perhaps he should ask Anna where you can go on dates but not with friends. Perhaps he needs to spend more time with people outside of campus. More time that is not a fake date.

            After a few more ear shattering screams from the girl behind him Castiel actually screams, moving closer and bumping shoulders with Dean. The man laughs and let’s go of Castiel’s hand to wrap an arm around his shoulders.

            “I thought you didn’t get scared during movies.” Dean whispers in his ear and Castiel frowns.

            “I do not usually. This movie is…very good.” He mumbles, making Dean laugh.

            “Yeah, that’s true.”

            “Hey, lover-boys, room for one more?” Gabriel whispers, moving his arm under Dean’s to get it off of Castiel. Who would have thought his brother would actually be so protective? Could it be he thinks the same of Dean that the older Winchester does of him?

            “Yeah, yeah, yeah, no touching and whispering in front of you.” Dean groans, raising his hands in surrender.

            The movie finishes soon after that and they head out of the theater, stopping outside of it to say goodbye. Again Dean is holding his hand, and again Gabriel is staring them down.

            “Well…I see you don’t like me with your brother, Gabe, shame I don’t care.” Dean says, and Castiel tries not to laugh at the irony.

            “Well excuse me for not wanting the resident player of our campus to go after my brother. Especially since he’s known for being _straight_. I can't help but think Dean has an agenda.” Gabriel explains, narrowing his eyes at the two of them. Dean rolls his eyes as Castiel begins to internally panic. He knows. He _knows._ Of course he knows, who is Castiel kidding? The trickster himself would obviously know when someone is pulling one over on him.

            “What do you want? Me to make out with him?” Dean asks and Castiel tries not to hyperventilate at the thought of making out with the older Winchester in front of his brother. Hell, doing it period no matter who was or wasn’t around is enough to freak Castiel out.

            “Don’t you dare!” Gabriel almost hisses.

Being the mature adult he so obviously is, Dean smirks and pulls Castiel to stand in front of him. Ignoring Gabriel’s complaints, Dean leans forward and kisses Castiel on the cheek. It isn’t mocking or rough like one would expect of an act done to piss off another person, Dean’s lips are light against his cheek. The kiss is actually sweeter than anything, which catches everyone off guard.

“Wow, my brother’s got it bad.” Sam muses, staring at them amused.

“I might,” Dean says, squeezing Castiel’s hand lightly before pulling him towards the car, “Not that Gabe would believe that.”

“You're damn right I don’t!” Gabriel calls, but as Castiel looks back at him, he can actually see the smile on his face.

This isn’t real. None of this is real and Gabriel is worried over nothing. Just like Dean is being counterproductive to his own mission in, well, everything he is doing. Sure, that kiss was nice and at nineteen it’s probably about time he actually had someone kiss him, cheek or elsewhere, but all of this is a waste of time. If it wasn’t for the food Castiel would be hightailing it right out of there.


	4. Unnecessary studying

**Summary for the Chapter:**

> Dean could literally hit Castiel with a bat that says 'I love you' and the idiot wouldn't get it

Castiel             has been bombarded with questions from Gabriel since the movie night, and quite frankly, yet again, he’s not sure it’s worth the free food. He stares down at his cell phone, frowning at the tenth text from his brother today as he paces the study room waiting for Dean. Today he’s going to be tutoring him and something else Dean refused to elaborate on. Of course before the other night that wouldn’t matter in the least, but ever since Dean went and kissed him on the cheek just the thought of seeing the man is nerve-wracking.

            “Hey, been waiting long?” Dean asks, grinning at him as he closes the door on Mrs. Flannery’s disappointing looks.

            “No, it has only been a few minutes.” Castiel lies, it’s actually been about thirty minutes, but Dean certainly does not need to know that.

             Looking at the pile of books Castiel brought Dean sighs, “So, Cas, you hungry?”

            “Do not try to escape before we even sta-wait….Cas? You're actually sticking with that nickname?” Castiel asks, trying not to sound excited. Of course Dean called him it the other night, but he figured it was in the excitement of the (albeit fake) date. He’s never gotten a nickname from anyone other than his brother and Balthazar, who teamed up on him and shared one. It’s truly exhilarating to have a special one from a special person.

            Not that Dean is special.

            “I-is it alright?” Dean asks, looking a bit embarrassed which is far too endearing for Castiel’s taste.

            “Yes, yes it’s perfectly fine.” He mumbles, staring at the books, “I…I like it.”

            Now beaming at Castiel, Dean moves in closer and sits down. “Awesome, so what homework will we be doing?”

            “Anatomy, perhaps?” Castiel muses, looking at the pile. He doesn’t exactly know what courses are necessary in Dean’s major of business and engineering.

            “Anatomy, huh?” Dean smirks as Castiel takes a sip of his hot chocolate from the café downstairs, “Isn't that better taught in the bedroom?” He asks, wiggling his eyebrows.

            Castiel quickly chokes on his drink, coughing some up on the table in a very unattractive way. Not that it matters what he thinks about Castiel’s level of attractiveness. Not at all. “Oh, my apologies…”

            “Whooaa! I’ve never gotten such a strong reaction to a joke before.” Dean laughs a little, wiping down the mess with a napkin Castiel brought up. “Sorry.” He mumbles, looking over to Castiel with a weak smile, “That kiss on the cheek made you pretty uncomfortable, didn’t it? You’ve been awkward ever since it.”

            “No, no, I'm not…it was just…my first kiss…of any kind.” Castiel says, trying to sound indifferent about it. “It’s nothing really, merely an alien action.”

            Dean smiles, relief evident in his eyes, “If anything is alien, it’s you Cas.”

            Castiel smiles back a little, “Yes that is admittedly true.”

            “I like that about you, though.” Dean admits, leaning forward in his seat, “You're undoubtedly a cool alien, like E.T. or something.”

            Castiel grins, “Sadly for you there will be no magical bike rides.”

            “Well look at you, Cas! Doling out a sense of humor!” Dean pats him on the back, “I didn’t know you had it in you.”

            Castiel raises a brow, “Dating a man you assume has no sense of humor is a strange approach.”

            Dean shrugs, “What could I say? You have a pretty face.”

            “I am a man, Dean, men do not wish to hear they are pretty.” Castiel points out as he grabs a book.

            “Sucks to be you.” Dean shrugs before Castiel shoves the book in front of him.

            “Name these tools.”

            “This isn’t anatomy.”

            Castiel tilts his head, “I know. I realized you do not take anatomy…”

            Dean smirks, “I wouldn’t mind a refresher.”

            “…Is this a flirtation…?” Castiel asks, his brows furrowed in confusion.

            Dean laughs, his eyes shining with affection. “It could be.”

            A lump suddenly forms in Castiel’s throat and he quickly stares down at the book, “Yes, well, I suppose even fake couples can share in flirtations…”

            Dean rests his cheek against his hand, “Who the hell calls it ‘flirtation’? You are seriously the strangest man I have ever met.”

            “But you do not seem to hate it, if I am not wrong.” Castiel looks at him amused, “Now stop trying to distract me. Get your work done.”

            “Whatever you say, mom.” Dean teases, bringing the book closer to read.

            After a few hours of studying, Castiel comes to the conclusion Dean does not, in fact, need a tutor. The man knows his stuff well. It makes no sense, though. Why would Dean want to waste half of his day studying with Castiel? It’s not like Dean enjoys studying. Well, honestly, no one enjoys studying.

            “Dean.” He calls, gaining the attention of the man across from him.

            “Yeah?” Dean asks, smiling at him, “What’s up, Cas?”

            “Why are you here?”

            “To…be…tutored, obviously…”

            Castiel furrows his brows, “But you do not need tutoring. You are an intelligent man, Dean. You understand engineering and business far better than I ever will.”

            A flash of something akin to fear flashes in Dean’s eyes before the man smirks at him. “Wow, a genius calling me smart, I’m honored.”

            “Sarcasm isn’t attractive, Dean.” Castiel points out, trying to stop his lips from curving up in a smile. He fails.

            “Your smile begs to differ.” Dean teases, leaning over the table to get closer.

            “None of this is answering my question.”

            “I have to study, so why not do it with you?” He asks and Castiel stares.

            “…But…why do it with me? I am not exactly the type of person you would normally hang out with, correct?”

            Dean looks at him annoyed, “Cas, this isn’t high school. Cliques and all that bullshit don’t exist. Well, I mean labels still do, but no one holds back from intermingling.” He crosses his arms, “It’s not the end of the fucking world for me to want to hang out with a nerd.”

            Castiel frowns, unsure if this is flattering or offensive. It sounded flattering, but he seems annoyed and even used the title ‘nerd’ which is not a kind word usually. “I suppose that makes sense. Such trivial things are high school mentality. However, people should share a common interest.”

            Dean laughs a little, “Oh don’t worry, I have an interest I think will keep us close for a while.”

            “Ruining my brother’s romantic relationship is not an interest we share, Dean.” Castiel points out, “Try again.”

            “We both like you.” Dean offers and Castiel smiles sweetly.

            “Thank you, I…like you as well.” Castiel admits, shyly.

            Dean smiles at him and gets up, “I guess that makes us friends now, huh?” He asks, grabbing his coat and an armful of books, “So as friends this time, let’s go grab dinner.”

            Castiel laughs quietly, “Dean, it is time for lunch, not dinner.”

            “Well whatever meal it is, I'm starving. Let’s go grab some grub.” Dean grins and Castiel nods, getting up and gathering the rest of the books.

            “I would not oppose food.”

            “It’s a date then.”

            Castiel falters, looking up at him in awe, “…What?”

            Dean blushes a little, “I-it’s just a turn of phrase.” He explains and Castiel blushes a little.

            “Right…yes, of course.” Castiel nods before the study room suddenly fills with a thick tense silence.

            Dean laughs a little awkwardly, “Right…so…want to invite Gabriel and Sam?”

            “Yes!” Castiel says a little too quickly, making the tense silence return for a moment.

            Well, this situation got really awkward really fast. Why does Dean have to be…so…Dean?

           

 


	5. Jealousy

**Summary for the Chapter:**

> Stupid boys getting jealous over stupid things and Meg enjoys causing drama.

            Castiel sighs, watching his brother stare at him suspiciously from across the dinner table. This impromptu not-double-date is going to be the death of him. Between the suspicious glances Gabriel is giving him and Dean, the curious stare of Sam's, and the overall awkwardness between himself and Dean at the moment this is undoubtedly the worst dinner he has had with Dean so far. He actually _misses_ studying, and, for that matter, his room.

            “So, Dean, you and my brother seem pretty awkward today.” Gabriel says bitterly, making them both choke on their drinks.

            “Well lucky me, a table full of handsome men.” A woman with bleached blonde hair says in a tone that suggests she’s being sarcastic before her eyes land on Castiel, “Hey there, I'm Meg, what’s your name?”

            “His name is Castiel!” Gabriel quickly pipes up, “He goes to college here, a real good kid, has a working cell phone and everything.” Castiel looks to his brother confused before Meg perks up.

            “Oh yeah?” Meg asks and Castiel simply nods.

            “Yes, well, we would like to order now if that’s alright with you, _Meg_.” Dean grumbles, staring the woman down.

            “Well then, by all means, order away pretty boy.” Meg mocks, earning a glare from Dean before they all order. Once she has all the orders she goes to leave, but not before winking at Castiel first. “I’ll be right back with your orders, sit tight sexy.”

            “She seems nice.” Castiel comments and Gabriel smirks.

            “You should date her.” The man teases.

            “He _can't_ date her.” Dean huffs, wrapping an arm around Castiel's shoulders and pulling him closer, “He’s dating _me_.”

            Gabriel groans and rolls his eyes, “Don’t remind me.”

            “Apparently I have to because you seem to forget. Consistently.”

            “I guess my mind just likes to block things I don’t accept.”

            Dean glares, “If only my mind were capable of that, I could forget you are friends with Sammy.”

            “Well you have to have a fully functioning mind. One that doesn’t live solely off of sex and booze for that to work.” Gabriel huffs.

            “Oh yeah, it requires the add-on of sweets, right?”

            Sam rolls his eyes, “Gabe, Dean, cut it out.”

            “Just go outback and whip them out so you can get this over with.” Castiel blurts out, remembering Balthazar saying something like that to some men who were fighting a week ago. It worked with them, but all Castiel seems to achieve with it is surprising everyone.

            “OH my _god_ he has been spending _way_ too much time you with!” Gabriel screams, “You’ve corrupted my baby brother!”

            “No more than you have corrupted mine!” Dean yells and Sam groans.

            “I'm not corrupted, Dean.”

            “I'm sure any corruption of Sam was in no small part your own fault, Dean.” Castiel points out, earning him a glare from Dean.

            “Whose side are you on?” The older Winchester practically growls.

            “The one that uses facts.” Castiel answers unfazed.

            “So neither side.” Sam teases.

            Castiel smiles at him, “Exactly.”

            Dean watches the two and sighs, “Life would have been so much easier if Sam had just befriended Cas.”

            Gabriel sighs as well, “Yeah, life would have been so much easier if you were not involved. I agree.”

            “Watch it.” Dean warns and Gabriel scoffs.

            “Hey there boys,” Meg greets before looking to Castiel, “Here’s your burger, hot stuff.” She winks and hands the rest of the boys their meals.

            Castiel smiles at the girl, thankful for the break in tension. Or at least verbal tension. He can practically feel Dean's anger from his spot near the window. “Thank you, Meg.”

            “Anytime.” She says before shooting a smirk at Dean and leaving.

            Castiel notices the unabashed look of anger on Dean's face and frowns. Meg is nice, he can't think of why Dean would react so negatively to her. Unless…she was one of his previous conquests. He is infamous for sleeping around, so it would make sense.

            “Hey, Castiel, is something wrong?” Sam asks, pulling Castiel out of his thoughts.

            “No…why?”

            Sam flashes him a concerned smile, “You just tore your napkin to shreds.”

            Castiel turns his gaze downward to see that he has, in fact, torn it to shreds. The idea of Dean and someone having sex has cause him to actually tear something to pieces. Of course a napkin is no big loss, but the fact he did it is a major concern.

“Huh…my apologies.” He says, putting it in his pocket to throw out later.

“What are you doing? Don’t put it there.” Dean groans, reaching into Castiel's pocket to pull it out. Castiel tries not to shiver, he does, but it happens anyways and Dean smirks a little. “The waitress is in charge of picking this stuff up. Let her deal with it.” He says, letting his fingers move from his thigh slowly.

Castiel swallows. Hard. Something else Dean notices. Fantastic.

“Dear god stop molesting my brother right in front of me!” Gabriel commands, reaching over the table to slap his hand away from Castiel.

“Alright, no one is touching anyone now, so can we just eat?” Sam asks, getting his fork and beginning to shovel salad into his mouth.

“Agreed.” Castiel mumbles before starting on his burger.

Their two brothers stare each other down for a few more minutes before eating their own meals. Once they start eating they stay quiet, no one looking at anyone else, until they finally finish and Meg comes with the check.

“So, Castiel who goes to college, does your working cellphone have room for one more number?” Meg asks and Castiel shrugs.

“My phone has a lot of empty room, one more number will not hurt it.” He answers, watching the cocky smile that comes to her lips.

“Excellent.” Meg writes her number down and hands it to Castiel before taking the money they give her and leaving.

“Well, we’re gonna go.” Gabriel says, getting up and helping Sam out, “We have plans that were rudely interrupted by our brothers.”

“See you guys later, have a nice night.” Sam smiles before leaving with Gabriel.

Castiel and Dean sit there for a little longer as the older man finishes his pie. Neither says anything and it makes Castiel uncomfortable. He knows Gabriel and Dean do not like one another, but he never actually seethes when Castiel's brother leaves.

“Dean…”

“Let’s go.” Dean stands up and heads for the door without looking at Castiel, making him grow more uneasy. Could it be he did something to upset Dean? He probably doesn’t want Castiel going after his previous conquests.

“I'm sorry.” Castiel mumbles, causing Dean to come to a stop and look at him.

“Do you know what for…?”

Blue eyes narrow as Castiel glares at Dean, “Do not talk down to me like a child, Dean. I do not need to apologize.”

“Oh no? Then why are you?” Dean asks, turning and heading towards Castiel.

“Because I have upset you with accepting Meg’s number.”

“You're damn right you did.” Dean grumbles, slowly reaching into Castiel's pocket and pulling it out as the boy mulls over his words. What right does Dean have to be upset about a past conquest? Castiel has more reason to be upset about Dean and Meg than Dean does about him and Meg. Of course Dean does not actually know that. Or maybe he does? He seemed to catch on to Castiel being nervous at his touching, which he is pointedly repeating. Perhaps that is an attempt to keep Castiel wanting him and away from Meg?

At that thought Castiel flies into a rage. Well, as much as Castiel is capable of. He quickly snatches the number back from Dean and shoves it back in his pocket, giving the now confused man a look that dares him to try and take it again. “I take it back.” He hisses, “I am not sorry that a previous conquest of yours is interested in me. There is no reason I should not take her up on the offer and call her, either. She is an attractive woman.”

Dean stares at him in a mixture of anger and confusion, “She is not one of my conquests, for one thing. Despite popular belief I have not slept with every woman in this town. And there is a definite reason for you to not take her up on her offer.” He grabs Castiel's two front belt loops and pulls him closer, an act the teen doesn’t fight as he celebrates the fact Dean has not slept with Meg. “You're dating me.”

Castiel looks up at him curiously. “Yes, but that is fake. As nice as it is to see my brother concerned about me, it is not real.” He brings his hands out to remove Dean's from his belt loops and pulls out the phone number, “But rest assured I was bluffing. I have no interest in her.”  Dean remains silent as Castiel tosses the number in a nearby trashcan. Castiel decides that’s a sign of his own victory.

“Just…just don’t date anyone while we are doing this.” Dean finally says, staring Castiel down, “That is the only rule I had when we started it and I'm not changing it now.”

“I will not be dating.” Castiel heads to Dean's car and mumbles under his breath, “No one but you.”

“What?” Dean asks, making Castiel's cheeks flush.

“Nothing. It was nothing. Let’s just hurry back so I can get homework done.”

A smirk comes to Dean's face, “You already finished your homework.”

“Th-then my…reading.” He finishes lamely and Dean stares at him for a long moment before finally turning away and starting the car.

“As you wish. Don’t want you to miss the excitement of reading alone in your room.”

Castiel shoots him an annoyed look, “Reading _is_ exciting, Dean.”


	6. Breaking point

**Summary for the Chapter:**

> Teenage angst intensifies

Castiel has known Dean for a month now as they play this pretend relationship game. Of course with each day it gets more and more uncomfortable for Castiel as he is, sadly, now developing feelings for the other man. It couldn’t even be a man he might actually have a chance with, either, it had to be one of the straightest men on campus. There is something severely off in his choosing of possible partners if the only person he has been attracted to is a straight man.

                “Say, Cas, how do you focus on reading so intensely? I mean I know it’s silent but I can’t even finish a page without needing to do something else.” Dean says, pulling Castiel out of his thoughts.

                “Well, it’s simple,” The teen begins, flipping a page, “I can focus on things longer than five seconds.”

                Dean huffs, “I can too, but it has to be fun stuff. Not this shit.”

                Castiel sighs and leans against the wall, “And what do you find fun?”

                “Sex.”

                “Yes, well, if sex can be used to help study, by all means, tell me what to do.” Castiel blurts out before going bright red, “Er, no, wait, I mean-!”

                Dean smirks, “Well if you’re offering.”  

                “I'm a guy, Dean.” Castiel points out, “I know you flirt with everyone, but please keep in mind my gender when you do that.”

                “You're the only guy I flirt with.” Dean says and Castiel stares at him in awe. It does not make him hopeful. Certainly not. Quite the opposite.

                “Why?”

                “Because you're the one I'm dating.”

                Castiel raises a brow and looks him over curiously, “But…not…for real.”

                Dean seems to grow uncomfortable at that and just shrugs, “Yeah, well, you're what I have right now.”

                “Ah, yes, best of a bad situation.” Castiel mumbles and Dean shakes his head.

                “What? No way! There is nothing bad about this!”

                Green eyes bear down on Castiel, who grows more confused by the second, “You have no problems pretending to date me while not having sex with women?” He tilts his head a little, watching Dean grow more uncomfortable. “Why…?”

                “B-because we will be pulling Gabriel and Sammy apart…” Dean murmurs and Castiel rolls his eyes.

                “If anything we have brought them closer.” He points out, “Taking them on double dates, you fighting with Gabriel so Sam rallies to defend him, giving Gabriel the hope that ‘if you can date mine, I can date yours’, and so on.”

                Dean laughs nervously, “Yeah, well, they still aren’t dating so that’s a win in my book.”

                Castiel shrugs, “You apparently have very low standards of success with this plan.”

                Lying down in the bed, his head near Castiel's lap, Dean looks up at him and smiles. “This is a pretty stupid plan, isn’t it?”

                Castiel nods, “I have only been saying that every day of the past month.” He grins, “At least once every day.”

                Dean sits up and stares at Castiel, “Hey, Cas…”

                “Yes?”  

                “Let’s….” The brunette falters, seemingly nervous, before he jumps off the bed. “Let’s go out tomorrow with them. Separate them once and for all.”

                Castiel rolls his eyes and reopens his book, “Alright. I have yet to go to-”

                “Nope! I already know where we’re going!” Dean grins at him, “Tomorrow we are taking them to…a haunted house. Halloween is coming up, they are opening them, and we are going.”

                Castiel raises a brow, “None of us scare easily…it will be a waste of money.” He thinks for a second before adding, “And if one of them does get scared they will end up clinging to the other. Seriously, are you even _trying_ to actually separate them? Because so far every little ‘double date’ has actually been quite romantic and unifying.”

                “Well, I guess I'm just too good at thinking of dates.”

                Sighing, Castiel stands up and goes to the door where Dean is now standing, “You're ulterior motives aren’t the ones you told me, are they?”

                Dean's eyes widen and he quickly grabs the door knob, “I don’t know what you're talking about, I _live_ to ruin their relationship. I hate your brother and I don’t want him around Sammy.” He nods to himself and opens the door, leaving as fast as he can.

                “I'm on to you!” Castiel calls from the door before closing it and going back to his bed. Okay, so he’s not 100% onto him, but he knows something is up. Tomorrow he is going to find out. Yes, he likes Dean, but he won't just sit back and not figure out what the man is doing. It is becoming alarmingly clear that separating their brothers is not his main goal.

                The next day they all meet up, in their own cars, at the haunted house that it turns out Dean's friend Charlie is running. Castiel has gotten to know her pretty well over the last month, but he cannot for the life of him figure out why she’s always staring at him and pointedly calling him ‘dreamy’ to Dean. All of Dean's friends are weird, though, so it’s fine.

                “Hey there Cas!” Charlie smiles at him before looking to Gabriel, “So this is the friend of Sam's? Dean he doesn’t seem like a horrible person!” Castiel looks at them curiously and Gabriel shoots a harsh look to Dean.

                “My god, even without me around you treat me like shit.” Gabriel groans, “If you hate me so much why do you keep inviting me and Sam out with you?”

                And there it is. The question Castiel has been expecting one of them to ask for the last month. For anyone whose motives are the ones Dean actually told him, this makes sense, but for two guys dating where one hates the other’s brother it is foolish.

                Dean crosses his arms, “I know how important it is for Cas that we get along, so I have been trying.”

                “You have _not_ been trying!” Gabriel says as Sam ushers them to the side so others can go in. “You are dating my brother. _Dating_. My _baby brother_. And he is borderline in love with you now!” He yells and Castiel's face goes bright red.  “I actually _have_ been trying for him, but you haven't! You are dating him but both of you seem awkward, like there is some sort of unresolved tension there. So why don’t you leave me and your brother alone for a night and fix the mess in this awful relationship you have!”

                Dean and Castiel look at each other guiltily for a minute before he turns back to Gabriel, “What would you know? You have been chasing my brother for how long now?”

                “Dean, Gabe, cut this out.” Sam says, going ignored.

                “It’s a hopeless endeavor.” Castiel mumbles, officially regretting this entire thing as Dean and Gabriel continue fighting.

                “…You two aren’t really dating, are you?” Sam whispers in Castiel's ear, making him tense up.

                “How do you-?”

                “The way you act with each other. There is obvious attraction, but you both act like you are too afraid to so much as look at each other.” The boy explains, smiling at Castiel. “I don’t know what you have planned, but I am pretty sure you need to talk about it soon…” He looks to their brothers and frowns. “And get our brothers away from each other.”

                “Dean I want you out of my brother’s life!” Gabriel yells, pulling Castiel and Sam's attention back to them, “You don’t deserve him and you keep fucking him up!”

                “I can be with Castiel if I damn well want to!” Dean yells back, “We are together and you need to accept that!” Without another word he makes his way over to their brothers silently watching them and grabs Castiel, grabbing the collar of his shirt and pulling him into a kiss.

                Castiel momentarily tenses up before going completely limp in Dean's grip as his tongue brushes over the still shocked teen’s lips. He doesn’t breathe, he’s not sure when he began to respond back, but they are actually _kissing_. Whether this is cause to thank his brother or yell at him, he’s not sure yet. When Dean finally pulls away, Castiel stares up at him in complete confusion, making the other man cough awkwardly.

                “Oh…shit…Cas, I'm so sorry…” Dean begins, looking down at him in horror as Castiel backs away. “I didn’t mean to…”

                Castiel snaps out of his daze. He didn’t mean to. Of course. Of course he didn’t mean to. It was an impulsive action to piss off Castiel's brother. “Yes, I know.” He says bitterly, “I understand you two don’t get along, but please stop dragging me into it.” After shooting Dean a harsh look he turns away from them and goes back to his own car.

                “Ah…son of a bitch. Cas, wait!” Dean calls and Gabriel huffs.

                “He doesn’t want you. Between his brother and some hot piece of ass, his brother will win.” Gabriel boasts and Dean glares at him.

                “That’s not what this is about you idiot!” Dean yells, jumping into his car and going after Castiel.

               

               


	7. Ending it

**Summary for the Chapter:**

> Dean should never be allowed to make his own decisions and someone needs to cue Castiel into human interaction

Castiel has successfully held himself up in his room for five hours now. Dean has only called once, which Castiel didn’t answer. In fact he won't talk to anyone but Balthazar, mostly because it’s his dorm he is hiding in, not even Gabriel because he is kind of mad at him too. Of all the things Gabriel's shenanigans have gotten him into, this is officially the worst. Is it an over the top reaction? Perhaps. Definitely. However, he needs to get his thoughts together.

He knows he needs to call off this whole charade with Dean, but every fiber in his being doesn’t want to. If it’s over, Dean won't see him. There will be no more dates or dinners or studying together, it will all just end. Of course Dean said he likes him, and had they not kissed with Castiel reacting in such a way, they could have been friends. Now it’s impossible though.

                “Cassie stop moping around and talk to him.” Balthazar groans, “I know you are new to the whole ‘feelings’ thing but you need to quit panicking like some hormonal teenager and do something about it.”

                Castiel looks to him wide-eyed and fearful, “But what do I do? Go up to him and say ‘sorry for ignoring you for three days but being kissed by you was both the greatest and worst thing to ever happen to me so I didn’t know how to deal with it’?”

                Balthazar shrugs, “That’s a start. An awkward start, but whatever. I'm sure you two are just going to be riddled with awkwardness when you start dating.”

                Castiel raises a brow, “What makes you think we will start dating?”

                “He kissed you. Straight guys don’t just kiss other guys.” Balthazar explains, “I would never kiss a guy. That’s for sure. Not even you with those ‘come hither’ lips.”

                “You are not funny, Balthazar.”

                “Yes I am, you are just in a shitty mood.”

                Castiel groans and throws himself on his bed, “That is true. I suppose I should just talk to Dean. He has not tried to contact me since that first night, though.”

                Balthazar scoffs, “Maybe because when he did call you ignored him and since then you have been hiding in my dorm room. You're lucky I didn’t tell Benny.”

                Castiel peaks over at him in fear, Balthazar and Benny have grown very close since this charade started, and Castiel would not put it past them to orchestrate a meeting between Dean and himself. “Thank you for not telling him.”

                A smirk comes to Balthazar's face and Castiel's stomach drops, “Oh but of course, Cassie. I would never _tell_ him.”

                Castiel pales, “What did you do?”

                Balthazar holds up his phone, showing a message to Dean with directions to his dorm room, “I texted Dean.”

                Before Castiel can yell at him or start hyperventilating someone begins to knock on the door, “You are evil.”

                Balthazar grins, “I am the best friend in the entire world.” He gets up and opens the door, showing a very out of breath and flustered Dean. “I’ll leave you two to it, but remember, no sex in my room. I'm a great friend but even I have limits.”

                Castiel narrows his eyes at Balthazar, “We are not going to-!”

                “Deal.” Dean cuts him off, closing the door when Balthazar leaves. “So…”

                “You kissed me.” Castiel blurts out, watching as Dean blushes.

                “I did.” Dean mumbles before looking to Castiel, “You ran away.”

                “I did.” They both go silent for a moment, until Dean finally speaks up.

                “Let’s break this off now.” He says, looking out the window, completely unaware of the way Castiel's heart just dropped into his stomach. “This was a stupid idea. I'm sorry for dragging you into it.”

                Castiel frowns, “It’s alright.”

                Dean looks at him confused, “Can I ask…why you even agreed?”

                “…About four years ago our mother and father died in a car crash. We got an inheritance and the life insurance, but apparently it is not wise to trust two teenage boy with finances.” Castiel explains.

                Dean stares in awe, “Why did you never tell me?”

                “It’s not something I advertise. Now if you will excuse me I am going to return to my room.” He says, before pushing past Dean and heading to his own dorm room again. Its times like these-well okay he has never had a time like this before but anyways -its times like these that make him thankful his roommate is always at his girlfriend’s apartment. Reaching his room he plops down on his bed. So, there goes Dean. He might come again out of pity, honestly, he saw that look in his eyes that he hates more than anything. The look that says ‘you poor thing, let me help you’.

                Castiel sighs to himself and sends Balthazar a text, telling him what happened and that it was safe for him to return to his room. After that he sends a text to his brother, telling him the truth. It’s only fair after all. Within seconds his brother sends a message back, apologizing for fighting with Dean and causing him trouble for the millionth time. He also adds on that he and Sam have been dating for two months which, admittedly, is a shock.

                The two end up texting back and forth, Gabriel effectively distracting him with his regaling’s of all their outings from his point of view. Talking about how hard it was not to hold hands with Sam or get jealous when others hit on him, and how badly he wanted to make a deal with Dean that ‘if you get mine, I get yours’. It would have been fair, had they actually been dating. An hour into their messaging each other there is a knock on Castiel's door. It’s quiet and he doesn’t recognize it as anyone’s he knows. He sends a text to Gabriel quickly before going and opening it, seeing Dean standing there awkwardly.

                “…Can I help you with something?” Castiel asks, genuinely confused. “Did you forget something here or-?”

                “I'm Dean Winchester.” Dean blurts out, silencing Castiel, “I have noticed you in the library a lot these past few semesters. I have been racking my brain thinking of how to approach you. In fact, because our brothers are friends, I even thought of luring you into a pretend relationship to woo you. No doubt that would work, right? But then I realized that if I were to kiss you in that kind of situation it might hurt you. Or me. Or both of us.” He says, an apologetic smile now on his face, “So that idea was obviously out. Then I decided to grow a pair and just come over here. So…while I'm not exactly an expert in dating, especially dating a guy, I was wondering…would you like to go out sometime?” He asks, grinning at the dumbfounded look on Castiel's face, “It’s on me.”

                “…Come again?” Castiel mumbles and Dean laughs a little.

                “Well, if you would like me to I could leave and return, but you only get a few of those a night.”

                Furrowing his brow, Castiel stares at Dean for a long few minutes before laughing.

                “Cas…?” Dean asks, looking at Castiel confused as the teen backs into his room, ushering him in between fits of laughter, “You know it’s not that funny…”

                “It is though, Dean.” Castiel says when he’s calmed down a little, “That was your reason? You couldn’t have just asked to hang out sometime as friends and let it go from there?” He smiles up at Dean, “You're weird.”

                Dean grins back, “That’s rich coming from you.”

                “Even I know how to properly approach someone you have feelings for.”

                “Oh? You mean running away when they kiss you and hiding in your friend’s dorm? Yeah, you're a regular Casanova. Wicked smooth.”  Dean teases and Castiel shrugs.

                “So…how come you never admitted this before? Surely you caught on to my feelings early on.” Castiel asks, making Dean look away in embarrassment.

                “I didn’t catch on to them at all until you ran off. Believe me, if I had, I would have acted way sooner.” Dean explains.

                “Huh.”

                “Yeah…”

                Castiel bites his lower lip, “Well then…I take it we are counting this as a clean slate?”

                “That’s right.” Dean says and Castiel nods.

                “So kissing before the first date would not be right.” He mumbles, watching Dean grow panicked.

                “Wait! No! Forget starting anew, we’ve been dating for a month now. Right? Right. Completely right. And let me tell you, we are due for a good kiss.” Dean says, coming up to Castiel and wrapping his arms around his waist. “And this time I'm keeping a hold of you so you can't run off.”

                Castiel blushes a little and smiles up at him, “Sounds fair enough.” He reaches up and wraps his arms around Dean's neck. “Lead the way, since you're the pro and all.”

                Dean frowns, “You need to stop listening to rumors.” He huffs before leaning down and kissing Castiel. It’s much slower than the last one, everyone’s tongues stay in their own mouth for what seems like an eternity until Castiel gets tired of it and takes the initiative. A low hum comes from Dean as he easily gains control again, kissing him until they both pull away for air.

                “So…you never cared about Gabriel and Sam's relationship?” Castiel asks, shooting him a glare, “All those fights were unnecessary?”

                “Oh no, I hate Gabriel more than anything in the world. However, I have faith that my brother won't date him.” Dean boasts and Castiel laughs a little.

                “Well do I have a surprise for you.”


	8. The real boyfriend

**Summary for the Chapter:**

> Where all sexual events transpire in two pages or less!

Castiel keeps a tight grip on Dean's arm as the man drags him through the hall towards Sam's dorm. “Dean you need to calm down.”

            “I will calm down after I have thrown my fist in your brother’s face!”

            “…Dean…” He sighs, allowing himself to be lead. Two nights ago they finally got together for real, and Castiel opened his big mouth and informed Dean that their brothers are dating. He had hoped there wouldn’t be a problem, but apparently Castiel has once again underestimated Dean's brother complex. It actually speaks volumes that Dean didn’t run off to kill Gabriel as soon as he told him and instead opted to stay with Castiel for two days straight. That’s probably the most dedicated Dean is capable of.

            Dean turns to look at Castiel, “Don’t give me that tone. I'm only gonna punch that fucker in the face once, because I'm a nice guy who doesn’t want to hurt you or Sammy.”

            “Because you’re a pushover who doesn’t want to piss off his new boyfriend and the brother he has an intense complex over.” Castiel corrects.

            “Ugh, I should’ve known a library nerd would be an ass.” Dean groans.

            “That’s what you get for stalking half-heartedly.”

            “It’s what I get for falling for a nerd.”

            Castiel's eyes widen as what Dean said sinks in, “…Falling…? You…um…”

            “Whoa, wait, no! Forget I said anything!” Dean stammers and before Castiel can tease him they are at Sam's door. Castiel swears the boy has some kind of sixth sense, too, because as soon as they get to the door it flies open to reveal the teen and Gabriel.

            “Must you two be so damn loud when you flirt?” Gabriel groans, “At least me and Sam no how to do that quietly.”

            “You're dating my fucking brother!” Dean accuses and Gabriel nods.

            “I am.”

            “And you kept it a secret so I wouldn’t kill you!”

            The older man sighs and shakes his head, “Not quite…”

            “It was my idea.” Sam admits from beside him, “I didn’t want to tell you, so I told him to keep quiet.”

            “I wanted to boast from the beginning.” Gabriel smirks, “But Sam wanted a while of peace before you found out.” He laughs a little as his gaze turns to Castiel, “Who would have thought we had a bargaining tool?”

            “I'm not a bartering chip to keep you from killing each other.” Castiel mutters, pouting at his brother.

            “Yes you are,” Gabriel teases, pinching his cheek, “And I love it.”

            “Dean, I love Gabe.” Sam confesses to his brother and Castiel can see the older Winchester holding himself back from punching Gabriel. The man has more control than Castiel gave him credit for. “Like you love Cas.”

            Castiel looks over at Dean with a smirk, “Even Sam knows. Still wish to deny it?”

            “Th-! I-! That is not the point.” Dean grumbles, “Let’s just go.”

            “Weren’t you going to punch my brother in the face?”

            “Not now! Later!”

            Castiel allows Dean to take his hand and drags him away from their room, “Well, um, see you two later I suppose…?”

            Sam laughs a little and waves to them before closing the door.

            “So what’s the plan now?” Castiel asks as Dean grumbles something under his breath, “Sounds interesting.”

            “Cas,” Dean begins, turning to look at him, “They are ahead of us.”

            “A…head of us?” Castiel's head tilts a little as he eyes Dean in confusion, “Ahead of us in what?” They both go silent for a few minutes until it finally clicks, “Oh, you mean sex.” He announces as they go into the room, “You…want to have sex?”

            Dean lets out a strange noise and moves away from him flustered, making Castiel wonder if this is actually the man known around school to be a Casanova of sorts.

            “Hmm…” Castiel begins, smiling at Dean's awkwardness as the man sits down on the bed across from Castiel's. “We have been dating for two days in a real, admit your feelings, kind of way…” He watches Dean slump a little, “But then again, we’ve been dating for a month as well. Not everyone starts dating with some kind of confession…a month isn’t too crazy to have sex…” Nodding to himself, Castiel sits down on his own bed and smiles at Dean, “Let’s do it.”

            “…Really?” Dean asks, blatantly shocked.

            “Really.” Castiel moves back on the bed, pressing up against the wall to give Dean room in front of him, “Come over here.”

            Dean moves over to his bed and climbs into Castiel's lap, pulling the younger man into a kiss. His hands moves from Castiel's shoulders to his chest, unbuttoning his shirt. Pulling away from the kiss, Dean laughs awkwardly, “I never thought I’d be nervous during sex again.” He mumbles, placing a small kiss to Castiel's jaw, “Not after my first time.”

            “This is your first time with a guy,” Castiel murmurs, tilting his head back to give Dean easier access, “It makes sense.”

            Dean makes a sound of agreement as he pulls Castiel's shirt off him, “Its a few firsts.” He admits, sitting on the heels of his feet as he yanks his own shirt off and tosses it to the floor.

            “A few…?” Castiel asks, genuinely curious. There are admittedly quite a few firsts one can have during sex, but just how much was Dean planning to do today?

            “First guy, first time waiting,” Dean begins as he removes their pants, “First person related to the person my brother is dating, first person I was _dating_ , first virgin…” He brings Castiel to lay down on the bed, his head comfortably placed on his pillow before Dean climbs on top of him. “First love.”

            Castiel stares at him for a second before laughing, “That is the cheesiest thing I have heard, Dean.” Grabbing Dean's arm to keep him from moving away in embarrassment, Castiel bring him in for a quick kiss, “And by far the cutest.”

            “Don’t call me cute, Cas, people have died for less.” Dean warns, bringing a hand to boxers.

            As soon as they come off everything becomes frantic. Hands and mouths desperately search out skin, trying to find sensitive spots to elicit moans from one another. It’s hot and close and all that’s in Castiel's mind right now is _Dean_ , everything that is Dean. His touch, his scent, his warmth, his _voice._ It’s intoxicating.

            “ _Dean_ …” Castiel moans, his face buried in his pillow as Dean turns him onto his stomach and presses himself between his thighs.

            “Cas…” Dean grinds into his thigh gap, moaning into Castiel's shoulder blade. They continue like this for a while, hips moving together in an increasingly fluid rhythm until Castiel feels the pressure building in the pit of his stomach.

            “Dean,” Castiel gasps, moving his hips faster to meet up with Dean's, “I can’t…I’m gonna…” A hand slides down between himself and the bed, grabbing at his already aching dick to pump it in rhythm with their hips. It doesn’t take long after that for Castiel to let out a low moan, arching back towards Dean as he cries out the older man’s name. He goes limp against the bed, shuddering every time Dean grinds his own dick against Castiel's from behind. It doesn’t take long, though, for Dean to reach his limit as well, moaning out Castiel's name as the teen’s bedding becomes even dirtier.

            Dean places one more kiss to Castiel's shoulder before rolling over to lay down beside him. “Wow,” He breathes out, shooting a grin Castiel's way, “We are definitely going to need to invest in some lube because _that_ is happening _a lot_ more.”

            Castiel stares at him wide eyed for a moment, just taking in the man’s overall disheveled appearance, before laughing. “I love you.” He blurts out, surprising Dean.

            “Oh, well, I guess that’s my cue to get the hell out of dodge.” Dean teases, sitting up and moving to leave.

            “You're not funny.” Castiel groans, grabbing his arm and yanking him back down, “You're staying right here, assbutt.”

            “Hah! The nerd _can_ curse!” Dean mocks, “Good to know what part of me matters most to you.”

            Groaning again, Castiel buries his face in his pillow, “For a popular guy, you are pretty lame, Dean.”

            Dean scoffs, “What would you know, nerd?”

           A/N: A story I wrote a year ago, right before Angels in the Kitchen. This is actually the third one I wrote but the second was so bad there was just no salvaging it so you don't need to see that mess. Instead, enjoy this mess! If you can.


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